From Downtown Winter Garden, Head West On Plant Street. Pass The Roundabout At Dillard Street And Continue Straight. Plant Street Becomes Oakland Avenue As You Enter The Town Of Oakland. Keep Going West For About 2 Miles. You’Ll Pass The Oakland Nature Preserve Entrance On Your Left. Shortly After, Look For 500 W Oakland Ave On The Right—It’S Near The West Orange Trail And The Old Oakland Town Hall Area.